4-butoxy-3-phenylsulfonylfuroxan | 1237752-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-butoxy-3-phenylsulfonylfuroxan
• 英文别名: 3-(benzenesulfonyl)-4-butoxy-2-oxido-1,2,5-oxadiazol-2-ium
• CAS: 1237752-66-7
• 化学式: C₁₂H₁₄N₂O₅S
• 分子量: 298.32
• InChiKey: KBSWKHHWTIRMAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  呋咱氮氧化物供体 、 正丁醇 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到4-butoxy-3-phenylsulfonylfuroxan
  参考文献：
  名称：

  Phenylsulfonylfuroxans as Modulators of Multidrug-Resistance-Associated Protein-1 and P-Glycoprotein

  摘要：

  A series of furoxan derivatives were studied for their ability to interact with P-gp and MRP1 transporters in MDCK cells overexpressing these proteins. 3-Phenylsulfonyl substituted furoxans emerged as the most interesting compounds. All of them were capable of inhibiting P-gp, and a few also were capable of inhibiting MRP1. Substituents at the 4-position of 3-phenylsulfonylfuroxan scaffold were able to modulate the selectivity and the intensity of inhibition. In some cases, they reverted MRP1 inhibitor activity, namely, they were capable of potentiating MRP1 dependent efflux. When compounds 16 and 17 were coadministered with doxorubicin, they restored a high degree of the activity of the antibiotic. Preliminary immunoblotting studies carried out on these two compounds indicate that they are capable of nitrating P-gp, which in this form is likely unable to efflux the antibiotic.

  DOI：

  10.1021/jm100066y

文献信息

• NITRIC OXIDE DONOR NEPRILYSIN INHIBITORS
  申请人：Theravance Biopharma R&D IP, LLC

  公开号：EP2855464A1

  公开（公告）日：2015-04-08
• [EN] NITRIC OXIDE DONOR NEPRILYSIN INHIBITORS<br/>[FR] INHIBITEURS DE NÉPRILYSINE DONNEURS D'OXYDE NITRIQUE
  申请人：THERAVANCE INC

  公开号：WO2013181332A1

  公开（公告）日：2013-12-05

  In one aspect, the invention relates to compounds having the formula: (I) where R1, R2, R3, R7, R8, Z, X, b, and c are as defined in the specification, or a pharmaceutically acceptable salt thereof. These compounds are nitric oxide donors and have neprilysin inhibition activity. In another aspect, the invention relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and processes and intermediates for preparing such compounds.
• Phenylsulfonylfuroxans as Modulators of Multidrug-Resistance-Associated Protein-1 and P-Glycoprotein
  作者：Roberta Fruttero、Marco Crosetti、Konstantin Chegaev、Stefano Guglielmo、Alberto Gasco、Francesco Berardi、Mauro Niso、Roberto Perrone、Maria Antonietta Panaro、Nicola Antonio Colabufo

  DOI：10.1021/jm100066y

  日期：2010.8.12

  A series of furoxan derivatives were studied for their ability to interact with P-gp and MRP1 transporters in MDCK cells overexpressing these proteins. 3-Phenylsulfonyl substituted furoxans emerged as the most interesting compounds. All of them were capable of inhibiting P-gp, and a few also were capable of inhibiting MRP1. Substituents at the 4-position of 3-phenylsulfonylfuroxan scaffold were able to modulate the selectivity and the intensity of inhibition. In some cases, they reverted MRP1 inhibitor activity, namely, they were capable of potentiating MRP1 dependent efflux. When compounds 16 and 17 were coadministered with doxorubicin, they restored a high degree of the activity of the antibiotic. Preliminary immunoblotting studies carried out on these two compounds indicate that they are capable of nitrating P-gp, which in this form is likely unable to efflux the antibiotic.